trans-Cinnamyl alcohol
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trans-Cinnamyl alcohol
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CAS No:
4407-36-7
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Formula:
C9H10O
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Chemical Name:
trans-Cinnamyl alcohol
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Synonyms:
2-Propen-1-ol,3-phenyl-,(2E)-;Cinnamyl alcohol,(E)-;2-Propen-1-ol,3-phenyl-,(E)-;(2E)-3-Phenyl-2-propen-1-ol;trans-Cinnamyl alcohol;1-Phenyl-1-(E)-propen-3-ol;(E)-Cinnamyl alcohol;trans-3-Phenyl-2-propen-1-ol;(E)-3-Phenyl-2-propen-1-ol;(E)-3-Phenyl-2-propenol;trans-Cinnamic alcohol;trans-3-Phenyl-2-propenol;(E)-Cinnamic alcohol;trans-1-Phenyl-1-propen-3-ol;trans-3-Phenyl-2-propenyl alcohol;(2E)-3-Phenylprop-2-en-1-ol;1613504-07-6
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CAS No:
Description
Solid
3-Phenylprop-2-en-1-ol is a reactant in the preparation of isobenzofuranones.
Liquid|Solid|White to yellowish crystalline solid, warm-balsamic, floral, sweet odour
Cinnamyl alcohol is a primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified). It has a role as a plant metabolite.|Cinnamyl alcohol is a naturally occurring compound that is found within cinnamon. Due to the low levels found in cinnamon, cinnamyl alcohol is usually supplied as [DB14184] within commercial products. Cinnamyl alcohol has been shown to be a skin sensitizer, with a NOEL (No Effect Level) of ~4%. Sensitivity to cinnamyl alcohol may be identified with a clinical patch test.|Cinnamyl alcohol is a Standardized Chemical Allergen. The physiologic effect of cinnamyl alcohol is by means of Increased Histamine Release, and Cell-mediated Immunity.
trans-Cinnamyl alcohol Basic Attributes
134
134.18
203-212-3
SS8YOP444F
623440|8775
DTXSID9041491
NEEDLES OR CRYSTAL MASS|WHITE TO YELLOWISH SOLID|WHITE NEEDLES FROM PETROLEUM ETHER
2906299090
Characteristics
20.2
1.9
1.0442 g/cm3 @ Temp: 20 °C
32 °C
248-252 °C
126 DEG C
1.599
FREELY SOL IN ALC, ETHER, OTHER COMMON ORGANIC SOLVENTS; SOL IN WATER, GLYCEROL; CLEARLY SOL IN 3 VOL 50% ALC
0.02 mmHg
ODOR OF HYACINTH|PLEASANT, FLORAL ODOR
BITTER TASTE
MIN CONGEALING POINTS SPECIFIED BY ESSENTIAL OIL ASSN: 33.0 °C FOR PURE; 28.0 °C FOR ALC PRISM; 20.0 °C FOR CINNAMIC ALC FROM STORAX|ALDEHYDE CONTENT: NOT MORE THAN 1.5% (AS CINNAMIC ALDEHYDE)|UV: 74 (Sadtler Research Laboratories Spectral Collection) /Cinnamyl alcohol (cis)/
Safety Information
GE2200000
IS OXIDIZED SLOWLY ON EXPOSURE TO HEAT, LIGHT, & AIR
P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P333+P313, P337+P313, P363, P501
H302
121.1164
|Warning|H317 (97.95%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501|Aggregated GHS information provided by 1908 companies from 22 notifications to the ECHA C&L Inventory.|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P333+P313, P337+P313, P363, and P501|Aggregated GHS information provided by 7 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
Drug Information
Cinnamyl alcohol is approved by the FDA for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.
Cinnamyl alcohol is 66% absorbed through the skin and shown to be rapidly absorbed from the gut.|Cinnamyl alcohol is metabolized and excreted primarily in the urine and, to a minor extent, in the feces. After oral or intraperitoneal administration to rats and mice, 76–77% of the dose of cinnamyl alcohol was recovered in the urine and feces within 24 h.|CINNAMYL ALC IS EXCRETED UNCHANGED IN NEUTRAL EXTRACT WHEN GIVEN TO RATS.
In general, esters containing an aromatic ring system are expected to be hydrolyzed in vivo. Cinnamyl alcohol is hydrolyzed to [DB14184].|ACIDIC & NEUTRAL URINARY METABOLITE OF CINNAMYL ALC WAS IDENTIFIED THROUGH A COMMON METABOLIC SCHEME.|Cinnamyl alcohol is a known human metabolite of beta-methylstyrene.
PATCH TESTS TO SEVERAL SCREENING SETS OF FRAGRANCE MATERIALS WERE PERFORMED ON 20 PERFUME-SENSITIVE PT. MOST COMMON ALLERGEN WAS CINNAMIC ALC (15 OF 20 PT).
3-phenyl-2-propene-1-ol
trans-Cinnamyl alcohol Use and Manufacturing
MEERWEIN-PONNDORF REDUCTION OF CINNAMALDEHYDE WITH ALUMINUM ISOPROPYLATE OR ETHYLATE; ALKALINE HYDROLYSIS OF STORAX; REDUCTION OF CINNAMAL DIACETATE WITH ACETIC ACID AND IRON FILINGS|OBTAINED ORIGINALLY BY SAPONIFICATION OF CINNAMYL CINNAMATE (STYRACIN). THIS METHOD OF EXTRACTION FROM STORAX IS STILL USABLE. SYNTHETICALLY, BY REDUCTION OF CINNAMALDEHYDE WITH SODIUM OR POTASSIUM HYDROXIDE.
Flavor and Fragrance
Air care products
100,000 - 500,000 lb|(1974) 6.81X10+7 G-CONSUMPTION IN FRAGRANCES|(1979) PROBABLY GREATER THAN 9.08X10+5 GRAMS
ASSAY: 98% MIN
All other basic organic chemical manufacturing|2-Propen-1-ol, 3-phenyl-: ACTIVE|WHEN SMALL AMT OF IMPURITIES ARE PRESENT AS IN NATURAL ARTICLE (CINNAMYL ALC FROM STORAX), IT REMAINS FLUID AT LOWER TEMPERATURES THAN THE MELTING POINT.|REPORTED USES: NON-ALCOHOLIC BEVERAGES 8.8 PPM; ALCOHOLIC BEVERAGES 5.0 PPM; ICE CREAM, ICES, ETC 8.7 PPM; CANDY 17 PPM; BAKED GOODS 33 PPM; GELATINS & PUDDINGS 22 PPM; CHEWING GUM 720 PPM.|FLAVOR USEFUL IN APRICOT, PEACH, RASPBERRY, PLUM FLAVORS.|OCCURS (IN ESTERIFIED FORM) IN STORAX & IN BALSAM PERU, CINNAMON LEAVES, HYACINTH OIL. OBTAINED BY ALKALINE HYDROLYSIS OF STORAX.|For more General Manufacturing Information (Complete) data for 3-PHENYL-2-PROPEN-1-OL (6 total), please visit the HSDB record page.
Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Masking
Flavoring Agents
Analysis Methods
| Name | Column Shape | Active Phase(℃) | Retention index | Temperature Control | Method | Comments | Reference |
|---|---|---|---|---|---|---|---|
| Kovats' RI, non-polar column, custom temperature program | Capillary | DB-5MS | 1302. | custom temperature program | 30. m/0.25 mm/0.25 μm, He; Program: 40C => 2C/min => 60C => 4C/min => 260C | Maia, J.G.S.Andrade, E.H.A.Zoghbi, M.G.B.Volatile constituents of the leaves, fruits and flowers of cashew ( Anacardium occidentaleL.)J. Food Comp. Anal.2000, 13, 3, 227-232. | |
| Kovats' RI, non-polar column, custom temperature program | Capillary | Supelcowax-10 | 2334. | temperature ramp | He, 35. C @ 5. min, 3. K/min, 200. C @ 20. min; Column length: 60. m; Column diameter: 0.25 mm | Wong, K.C.Teng, Y.E.Volatile Components of Mimusops elengi L. FlowersJ. Essent. Oil Res.1994, 6, 5, 453-458. | |
| Kovats' RI, non-polar column, custom temperature program | Capillary | DB-1 | 1278. | temperature ramp | 25. m/0.2 mm/0.33 μm, 4. K/min; Tstart: 50. C; Tend: 300. C | Osorio, C.Alarcon, M.Moreno, C.Bonilla, A.Barrios, J.Garzon, C.Duque, C.Characterization of Odor-Active Volatiles in Champa ( Campomanesia lineatifolia R. P.)J. Agric. Food Chem.2006, 54, 2, 509-516. | |
| Kovats' RI, non-polar column, custom temperature program | Capillary | HP-5MS | 1310.1 | custom temperature program | 30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min) | Andriamaharavo, N.R.Retention Data. NIST Mass Spectrometry Data Center.NIST Mass Spectrometry Data Center, 2014. | |
| Kovats' RI, non-polar column, custom temperature program | Capillary | DB-5 | 1303. | custom temperature program | 30. m/0.25 mm/0.25 μm, He; Program: 40C(2min) => 4C/min => 220C => 20C/min => 280C | Andrade, M.S.Sampaio, T.S.Nogueira, P.C.L.Ribeiro, A.S.Bittrich, V.Amaral, M.C.E.Volatile compounds of the leaves, flowers and fruits of Kielmeyera rugosa Choisy (Clusiaceae)Flavour Fragr. J.2007, 22, 1, 49-52. |
Computed Properties
Molecular Weight:134.17
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:134.073164938
Monoisotopic Mass:134.073164938
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Complexity:101
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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